Date Night – What Should You Wear?


I’ve been on countless dates over the years and one of the most critical and stressful parts of the date is the hour leading up to the date night when I’m trying to figure out what to wear.  I want to show my date that I have style and class, so I know that I can’t just wear a tee shirt and jeans and hope for the best.  I also have to be conscientious of what shoes I wear. 

A friend once told me that she can tell a lot from a guy by his shoes and that is one of the first things she looks at when going on a date.  If a guy’s shoes are old and ratchet, he’s either too poor to buy new shoes and isn’t in a position to be dating, or he just doesn’t care enough about himself, so does that mean that he won’t care that much about his date? 

What Should You Wear?

It has always been my practice to ask my date what she is going to wear when making plans for the evening.  If we plan on going to a nice restaurant and hitting a bar afterward, then I would plan on wearing a button-up untucked shirt, straight leg jeans, and maybe my red Adidas sneakers or my brown Johnston & Murphy boots (For more information on what shoes you should have in your closet, check out my post How Many Shoes Should a Guy Own). However, if I am meeting for cocktails after work I would stay in my suit and just lose the tie. You can never go wrong wearing a two-piece suit, it is always certain to impress.

Nowadays I don’t have to think as hard when dressing up (or down) to go out. I just ask my fiancée what she wants me to wear.  She gives me some ideas and I go from there.  Although I really appreciate her input, I still think about my style and how I want to be perceived.  I’m not talking about the perception of other ladies, but more so a general overall perception.  I want people to think, man that dude has style. Maybe they will say something like I really like his boots, or those two make a super cute couple. 

Looking Great

I was taught from a young age that you never leave the house looking less than perfect.  Don’t get me wrong, there are plenty of times I just throw on a hat and my beat-up Chucks to head to the store. I just make sure that I wear clean underwear and an outfit that is presentable. You never know when you might run into your boss or your next date.

Style Resources

If you have a super tough time trying to figure out what to wear on a date, there are plenty of resources out there to help you come up with something.  One of the best resources is having a gay best friend.  He will always give you the honest truth about what you have on and whether or not you should change.  If you don’t have access to a gay BFF, the next best thing is a clothing subscription box, like Trunk Club

Trunk Club matches you up with a personal stylist and picks out what they think will look great on you. Your new threads are then delivered right to your door.  Pretty convenient right? The best part is, you only pay for what you want to keep.  I wish they had these services 10-15 years ago, I may have picked up some better quality dates. 

Nevertheless, finding the right outfit for your night out can be tough, and the best advice I can give you is to ask for help if you’re unsure, then go with what you think would “wow” your date.  Remember to always dress to impress!

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